Need a flexible short-term rental in Shelter Island? Browse fully furnished stays tailored for extended holidays, digital nomad bases, or business travel. Compare verified options to secure a convenient setup for your visit.
Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings
Exceptional
1 reviews
AC, Barbecue, Crib, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Internet
Internet, View, Fireplace/Heating, Air Conditioner, Guest Services, Parking, Security/Safety
Fabulous
17 reviews
AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen
Exceptional
23 reviews
Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay
AC, Dryer, Internet, Laundry, No Smoking, Pool, Washer
Laundry, Wheelchair Accessible, Pool, Parking, Internet, Child Friendly
AC, Arcade, Balcony, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry
Exceptional
6 reviews
Apartments, Accommodations, Parking, Spa, Lodgings, Vacation rentals, Places to stay, Family
Exceptional
14 reviews
AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area
Exceptional
55 reviews
Apartments, Accommodations, Parking, Spa, Lodgings, Vacation rentals, Places to stay, Family
Exceptional
2 reviews
AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen
Exceptional
29 reviews
Accommodations, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals, Places to stay
AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet
Accommodations, Pools, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay
AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen
Exceptional
35 reviews
AC, Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Internet, Kitchen
AC, Balcony, Barbecue, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave
Exceptional
12 reviews
Barbecue, Dryer, Free Parking, Heater, Internet, Laundry, Living Area, Microwave, No Smoking
Superb
3 reviews
AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave
Exceptional
33 reviews
AC, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Internet, Kitchen
Exceptional
2 reviews
Pro Tip:
OwnerDirectVacationRental aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Short Term Rentals in Shelter Island.
OwnerDirectVacationRental can help you find hotels, resorts, and rentals near many of 's top attractions, neighborhoods, and points of interest.
What makes our short term rentals stand out?
Every short term rentals shown on Owner Direct comes from trusted travel sources and verified hosts, so you can browse with confidence.
Compare a range of properties and find fair, transparent pricing—no hidden fees.
From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.
Some of the best short term rentals in Shelter Island are:
There are a lot of options in Shelter Island. If you plan on staying in the Shelter Island area, consider making a reservation for a few nights at one of these properties as these have been rated the top Short-term Rentals in Shelter Island
You can explore 623 verified short-term rentals in Shelter Island, including apartments, houses, and furnished stays suitable for both travel and temporary living.
Short-term rental prices in Shelter Island vary depending on location, property size, and travel dates. Rates typically start from around $208 per night, with higher prices for premium properties or peak seasons.
Many short-term rentals in Shelter Island include Wi-Fi, making them suitable for remote work. Some listings also provide dedicated workspaces, but it is recommended to check property details for specific features.
Booking 30 to 45 days in advance is generally recommended for the best availability. For peak travel periods or major events in Shelter Island, booking earlier can help secure better options.
In many cases, utilities such as electricity, water, and internet are included in the rental price. However, this can vary by property, so it is important to review the listing details before booking.
Short-term rentals in Shelter Island often include amenities such as Fireplace/Heating, Laundry, and Wellness Facilities, providing a comfortable and convenient stay.
Short-term rentals in Shelter Island are often used for flexible stays, including work trips or temporary housing, while vacation rentals are typically geared toward leisure stays in tourist areas. Both offer furnished, home-like accommodations.